


When It's Right, It's Right

by 5datesor2000dollars



Category: Gilmore Girls
Genre: Destiny, F/M, First Time, PDLD, not who you thought it would be
Language: English
Status: In-Progress
Published: 2017-09-06
Updated: 2018-03-19
Packaged: 2018-12-24 12:11:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 11
Words: 19,542
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12012453
Author URL: https://archiveofourown.org/users/5datesor2000dollars/pseuds/5datesor2000dollars
Summary: This starts off at "Wedding Bell Blues"Rory and Logan start out the way they did on the show. However Rory is still a virgin and Logan is not a big fan of being someone's first- he can't handle the emotional baggage that tends to come with it. Rory knows Logan won't stick around if she's still the big V which leads us to her trusty friend Finn. He's been helping her out with a class they take together and they spend a lot of time together, and share common interests.How will things play out with Rory and Logan and will Rory see the caring and kind guy who's been there all along?





	1. 1

**Author's Note:**

> So I read a bunch of other fics that led me to this idea. I love Rory and Logan together in the show but the thought of Finn as a romantic interest was intriguing. It's my first time writing for Gilmore Girls, it's a weird topic and it's my first narrative (all in Rory's POV- imagine it like a blog entry of sorts) so please, please be kind :)
> 
> This is slightly AU and Rory is not the prude she seems to be on the show  
> Any and all feedback is appreciated.
> 
> Some chapters will be pretty short and some quite long, please bear with me!
> 
> I had help with editing and such from a great writer whose work you can check out on FF.net AshleyWheeler1

**Notes for the Chapter:**

> Sept 11- made a few changes in the earlier part of the chapter. Sorry if you thought there was an actual update!

   

“Oh my God!” I groaned out loud as I grasped my head in my hands.

What the hell was I thinking? “I just want to know what it would be like” why would I say that? UGH!!

And what did I say about stringless fun? God, I am such a hypocrite! What was I thinking, making out in a dressing room at my grandparents vow renewal!? I mean, I was actually going to have sex with him!

In hindsight, thank God Mom, Luke and Dad all walked in, or else I would have... lost... my… (Great! And now I’m hyperventilating!) virginity! In a public place… at a family event… to LOGAN HUNTZBERGER!

We barely know each other, and yeah he’s gorgeous... and funny... and smart... And he’s been a really good friend lately, especially since the Male Yale Meat Market party. But, no! That's not why I’ve waited this long, to just give it up in the heat of the moment, all because my body wanted to! No! I want it to actually mean something!

It had already been a week since the vow renewal, and I had thought the intensity of the moment with Logan had worn off, but clearly it hadn't. We had gone for coffee last night, and when he dropped me off at my dorm he practically took my face off with the force from which he kissed me. Our pulses were racing, our tongues duelling... we had stopped to catch our breaths, and I took the break as my opening to cut the evening short.

I hadn’t had the guts to renege on my proposal to him, but I really didn’t want to bare the truth to him just yet.

 

* * *

 

   

Over the next month or so, Logan and I had hung out a few times, mostly in a group with Colin, Finn, Steph, and Juliet. It was always nice hanging out with the whole gang, because they were so fun, and didn't take things too seriously - which, let's be honest, I could use a few more people like that in my life!  

Every time we met up they had a million tales to tell me; like the time they broke into someone’s estate in Martha’s vineyard and ended up skinny dipping in their pool only to be caught and chased off the property leaving their clothes behind.

Let’s not forget the time the girls kidnapped me and stuffed me on a helicopter with them so we could “avoid the traffic” getting to New York City. Once there, Juliet and Steph put us up in the most lavish and expensive hotel they could find and then proceeded to burn holes in their credit cards buying all 3 of us a wardrobe's worth of new clothes and shoes. I can’t say I was comfortable with this but they wouldn’t take no for an answer.

Sparing no expense there were always excursions like massages and concerts as well as good old-fashioned girl time sitting around talking and painting our nails. Now they might not be as grounded as Lane or as intellectual as Paris, but Steph and Juliet were pretty great girlfriends and they were always up for a good time. In all honesty without my mom around all the time they were decent proxies for the honorable Lorelai Gilmore.

Then there’s Colin who was always up for a good debate, he was a great sparring partner; if only he could keep his elitist points of view to himself and conjure up a valid argument then maybe I would feel like I had some actual competition.

In the end, it was always good fun because it didn't matter the topic Colin somehow always ended up with his foot in his mouth. At which point Logan and Finn would automatically jump in, taking advantage of their smart-mouthed friend's ability to get flustered and razz him to no end. Which made Colin even more red-faced and agitated and usually the night would come to an end with all of us in stitches, laughing over Colin’s inability to compose himself.

However, the biggest surprise to me was the friendship I had formed with Finn.  It seemed that we had more in common than anyone would have ever guessed.  He grew up in society, but he wasn’t raised with his nose in the air, and he had an actual aspiration to take over the family business and to be successful at it. He also took his studies pretty seriously, although he would NEVER say it out loud… you know, because he has a reputation to uphold and all.

It took me forever to pinpoint it but Finn reminded me a lot of my mother- short skirts and lipstick aside, well wait come to think of it they did have similar taste in nail polish colors, but that’s another story. But seriously he was fun loving, energetic and could reference movies and music at the drop of a hat. Finn was a ball of energy much like my mother and enjoyed life to the fullest.

The thing I loved most about Finn though was his ability to make me comfortable, there were often time when the girls, or Colin or hell even sometimes Logan would make me feel small for not having lived enough, or taken enough chances and Finn would sense my discomfort and manage to change the subject or remind them “Well that’s why she’s got us” or “maybe we’re the lucky ones since she’s the only one with a head on her shoulders, Lord knows where we’d be without her” he would say

Then there were the many times Steph and Juliet insisted on doing a makeover on me and while I was feeling shy and embarrassed Finn would pipe up “What does she need a makeover for, she bagged Hunztberger didn’t she” I recall him saying one night.

It never failed, anytime he paid me the smallest compliment I blushed like a teenager who’s crush had said just said hello! Finn just let me be myself and he accepted me for who I was. Which when I think about it even Logan tried to get me to change or mold me to fit into his circle better, but not Finn he just let me be.

Not only had my and Finn's friendship grown, so had my relationship with Logan. We had gone out on a few dates, usually ending up with a heated make out session against my dorm room door. We were both really busy though; I had the newspaper, finals were coming up and family time. He had finals as well, plus, well… there was also Sarah, Julia, Tiffany and wait - who was the blond…? Oh yeah, Jessica.

Truthfully I didn't mind him seeing other girls really… Why. You ask? Well, honestly, because it took a lot of heat off of me and the fact that I hadn’t ended up in Logan’s bed yet. I was still trying to justify losing my V-card to a guy I wasn’t in a serious relationship with. Yes, I liked him - A LOT - but deep down, I just couldn’t bring myself to do it.

The problem was, I knew that if I told Logan I was still a virgin, he would leave me in the dust so fast my head would spin.

Yes, he told me time and time again how special I was to him - that he had never had a connection with a girl like the one he had with me… did that make me want to forget everything and ask, no, beg him to ravish me, but I didn’t. 

But, it did make me feel like it was not all wasted, that maybe eventually I would be able to be with Logan even if there were no labels attached.

Deep down, I knew that if I was really that special to him that he would give up the harem and tell me that me being a virgin wasn't as big a deal to him as I was making it out to be, but I just couldn’t bring myself to do anything about it either way.


	2. Chapter 2

**Notes for the Chapter:**

> So I pretty much re-wrote this whole chapter. Some things I replaced completely, or they will be in the next chapter since I added so much more to it.
> 
> I know some of the formatting is a little off, but I just couldn't figure it out.

The new semester started, and I felt a new energy that I hadn’t had before. I was doing well in school; I had friends - like real, legit friends; Mom and Luke were good... the only gray cloud hanging over my head was that Logan and I were still seeing each other.    
  
By this point we had even been seeing each other partially naked - I had finally opened my mouth and told Logan that maybe I had dug myself a bit of a hole the night of the vow renewal, that while I was still good with no strings, I wasn’t quite ready for the whole nine yards. He said that was cool, but he didn’t see why we couldn’t do “other things” while we waited for my head to catch up with the rest of my body. Before I knew it, we were groping each other, I was giving him hand jobs, blow jobs, etc.    
  
Just last week, I managed to stifle my insecurities and let Logan go down on me. Jess had tried once, but I squirmed and bucked so much that he ended up with a black eye, hence ending all his forays into pleasuring me.    
  
But oh, by the way, the whole tongue thing...down there…. not overrated...at all! Maybe it’s all due to experience or maybe Logan is just a natural. In any case, I never thought I would be one to be comfortable with having a guy's face down there but I have never felt this way before. He was so delicate but skilled and thorough that every stroke of his tongue was like kindling being thrown on an already blazing fire; at times it was almost unbearable but I never wanted him to stop. It made me feel so sexy and turned on, that I couldn’t wait for him to do it again. 

With the new semester came another new discovery for me...economics...not my forte, but lucky for me, Finn and I were in the same class.

I somehow managed to convince him to tutor me - yeah, I know, I would've thought that the roles should be reversed, too, but it was Logan’s suggestion and I really needed these credits so I did what I had to do. 

Now when I say I had to convince Finn to tutor me, I mean it. It took some real arm twisting to get him to agree. As I said it was Logan’s suggestion and since only Finn’s closest friends knew that he was a closet econ whiz - It was bred into him at an early age, you know preparation for taking over the family business and all.- I was able to use that to my advantage. There were lots of promised pitchers of beer and chicken wings to sway him but finally, he agreed...on one condition.

The condition was I had to swear on my mother’s grave that I wouldn’t breathe a word to anyone outside of our little circle. He was adamant that it would ruin his reputation with the ladies since the girls he tended to attract couldn’t tell the difference between an accountant and a CEO they would just assume he was boring, which in Finn’s mind, of course, translated to boring in bed and not give him a second thought.

Which is crazy, because if you’ve spent 5 minutes with Finn you’d know he’s anything but boring… The bedroom part I’m not sure about. I’m not saying I understood his logic but I swore I wouldn’t tell a living soul.

  
Often, Finn and I would go find a private room at the library so our crazy roommates couldn’t distract us - and by that I mean Logan since he, Colin and Finn all shared a place. It was inevitable that once I set foot in the door Logan would be all over me. We learned our lesson after the third try.    
  
The first time we showed up at the guys place I sat down on the couch with Finn across from me on the lazy-boy, shortly after we opened our books Logan came in and sat down right next to me, not leaving any room for personal space. He proceeded to rub my shoulders and neck, massaging out all the stress from the day. As much as I was trying to pay attention to what Finn was saying, Logan’s hands were working wonders on my stiff neck and it was relaxing me a bit too much and I started to fall asleep; so Finn and I decided to call it a day.   
  
Our next attempt was brought to an abrupt halt when Logan exited the bathroom after his shower in nothing but a towel. He didn’t even have the courtesy to put clothes on before he plopped down beside me and started running his fingers through my hair making me shiver at his touch. Finn could tell I was trying not to crack under Logan’s advances, so he quickly got up from his chair and sat between us, forcing Logan to the edge of the sofa. I shot Logan an apologetic look but really I was grateful that Finn stepped in. I managed to get a grip on myself enough to finish studying for our quiz the next day, but my attempts at composure were becoming more and more futile.   
  
And that was proven the third and last time we studied at the guy's place. When Finn and I arrived at his place Logan was already seated on the couch with a coffee in hand. As I approached to give him a kiss hello he raised the coffee cup to my nose, as I took a whiff he said “ smells good, doesn’t it Ace,” he teased. As I went to reach for the cup Logan pulled it away and with his other hand pulled me down on the couch next to him. I landed hip to hip with him and he immediately leaned in and started kissing my neck.

I was caught slightly off guard at first but when I realized he wasn’t going to stop at just necking I pushed against his chest “come on Logan, stop I have studying to do” he then moved his lips from my neck to my mouth “what Ace, I’ve missed you” he whispered between kisses. Before I could shove Logan off of me Finn returned from the kitchen where he had been getting drinks and a snack for us, per our usual routine. We were only made aware of his return to the living room by his shrill “ What the hell, mate!” coaxing us to pull back from each other.    
  
Finn marched over to us and in one swift movement handed me the coffee cup Logan was miraculously still holding and then yanked Logan up by his arms and forced him towards his room. Yelling at him “I can’t believe you two but mostly you Logan it was your suggestion that I help Rory with her classwork and now every time we’re here you find some way to distract or interrupt us.”

  
Logan’s attempt to move and return to his place next to me on the couch was impeded by an exasperated Finn as he continued to chew out Logan “ You mister have bothered us for the last time today! Now be a good boy and stay there til we're done” he exclaimed pointing to Logan’s room.

  
As Logan looked back at me pitifully I couldn’t help but snicker at Finn’s parent-like tirade.    
  
We managed to get some studying done after all, but after that night we decided the library or my place would be best if we wanted to get any work done.


	3. Chapter 3

**Summary for the Chapter:**

> So this chapter has been re-written. I was premature in posting and added a lot of content so it bumped some stuff back.
> 
> Sorry if this caused confusion, but I didn't want to delete the whole story so I'm writing over it as I go.
> 
> Still, I hope you are enjoying.

Over the next month, I learned that Finn and I had a great many shared interests; among them a love for the band Descendents and all things Johnny Depp among others.

I found this out one night when we had been studying together at my dorm and a preview for the new ‘Charlie and The Chocolate Factory’ remake came on Access Hollywood.

“Oh my gosh, I can’t believe they’re remaking a classic like Charlie and the Chocolate Factory,” I said in awe. “Normally I’d be worried about a remake, especially one so near and dear to my heart; take Bewitched, for example, it was just awful. But I think with Johnny Depp headlining, it's bound to be amazing. I love Johnny Depp.” I continued excitedly

“Of course you love him, he’s Johnny Depp, the man can do no wrong!” Finn exclaimed “No, Finn, you don’t understand Charlie and the Chocolate Factory is my favorite movie of all time and my love for Edward Scissorhands is unparalleled,” I said defensively. “Well Love as much as you might love that movie I’m practically Johnny Depp incarnate,” Finn said as he waved his black fingernails at me. “Besides I look way better in eyeliner!” he said victoriously.

I couldn’t help but laugh “Oh Finn, you think you’re so eccentric, such a misunderstood, lost soul; but really you’re not. You’re a little strange, I’ll give you that but you have tons of friends, and the only thing misunderstood about you is that you’re actually super intelligent… but you play the dumb surf bum part really well.”

“Ah Love you wound me” Finn replied sarcastically “there are lots of things you still don’t know about me darling, don’t be so quick to judge...I’m as eccentric as they come. But all tiffs aside we’re going to see this movie together right?” he asked hopefully.

“Finn, it doesn’t come out for another 4 or 5 months, I’ll be back in Stars Hollow for the summer and you’ll be where Australia...Bora Bora? It’s a sweet thought Finn but we both know with the way you drink you won’t remember you said this. You’ll end up taking some flighty red-head and will have forgotten all about this conversation” I contested.

“Oh ye of little faith Rory, like I said there’s a lot you don’t know about me; like the fact that I have an exceptional memory despite my fondness for whiskey. Besides you’re hardly forgettable Kitten so mark it on your calendar!” Finn replied and I turned 2 shades of red at Finn’s subtle flirtation.

Aside from movies and music Finn as well as having an appetite for alcohol, the boy could also eat! I’ve seen him scarf down 30 chicken wings and a plate of fries, and then 2 hours later polish off a 10-inch pizza I seriously think I might have met my match. When I inquired about how he could eat so much and not gain a pound he replied vaguely “I burn it all off Love” I was confused and when I mentioned that he didn’t strike me as a gym rat” he smirked at my naivety “Oh Rory, there are many other ways to burn calories than the gym, and much more enjoyable might I add” he said suggestively. All I could think was ‘that’s  _ a lot _ of sex’.  In the end, though you’d never know that he ate like that and drank like a fish because; to put it lightly the boy was fit. I mean washboard stomach and all.

How do I know this, you ask...

Well, once I was waiting for him in the common room of his dorm while he went to change his shirt before heading out to the library and WOW!  I needed to pick my jaw up off the floor after that show.  Finn being Finn, saw my reaction and grinned like the Cheshire cat at me.  He shrugged his shoulders, grabbed his messenger bag and just proceeded to walk out the door - leaving me standing like an idiot in a puddle of my own drool.

Yes, Finn was hot, but I had never really given it a second thought; since Logan was always the one making himself noticed to me. Maybe it was the fact that it was a mutual attraction… that made it so easy, but recently I was beginning to wonder why girls practically fell over themselves for Logan when there were two hotties standing right next to him.

  



	4. Chapter 4

On this particular night, the library was packed and we couldn’t find a quiet place to study.  Colin had Steph over at the guy's place - so you know damn well they’re not gonna be quiet.  

I checked to see if Paris was home in our dorm, and she informed me that she was going out with Doyle, and so we would have the place to ourselves.

When we walked in, I told Finn to make himself comfortable, while I went and got us snacks and drinks. When I came back into the room I noticed Finn had taken my instruction to get comfortable to heart; he had removed his shoes and socks and was in the process of unbuckling his belt. “Whoa there buddy, I don’t know what you think is going to happen here to tonight but you can buckle that belt back up right now,” I joked. Finn just grinned “Well if I know you, this is only round 1 of many more of snacks to come so I just making room” he replied lightly.

  
We had been studying for about 2 hours and we needed a break, so I put on a pot of coffee and brought some cookies that Sookie had given me last time I was back home.  I set the coffee and cookies on the table and took my seat back on the couch.  
  
Finn pulled his flask out of his jacket pocket and proceeded to make his coffee a little more Irish.  I had taken a bite of one of the chocolate chip cookies, it was so chewy and chocolatey and tasted like heaven that I may have let out a louder than necessary moan of appreciation.  
  
Finn just looked at me and cocked his eyebrow and said: “now I know why Logan keeps you around.”  
  
I was shocked at his remark, and couldn’t help it that my face was turning all kinds of red. I had placed my hand over my mouth to keep the cookie crumbs from falling out, making me unable to respond.  Finn looked at me with a mock sympathetic look.  “No need to be embarrassed, Love.  We all know what you two get up to when the doors are closed,” he said.  
  
I had finally managed to swallow the cookie and before I knew what I was saying I looked at him indignantly.  “Oh you do, do you? You think you know everything” I said, and rolled my eyes.  
  
Finn took a sip of his coffee and turned to look at me, confusion and curiosity all over his face. He placed a hand on my knee and asked “Love is there something more you’d like to share?  ‘Cause from experience, those sounds are only made when two people are getting carnal in between the sheets and - well - apparently when one is eating a sinfully delicious chocolate chip cookie.” He said.

I was still red in the face and couldn’t seem to come back with a good retort.  Who thought I would ever get beat at my own game, but I was stumped!  I didn’t want to dig myself a hole, but at the same time, I didn’t see the point in trying to hide the truth.  
  
I had a feeling Finn would figure it out sooner or later, so I let his comments slide and shoved another cookie in my mouth - chewing and swallowing with a vengeance - and looking anywhere but at Finn.  
  
That’s when it hit him.  I thought his eyes were gonna fall out of his head, they bugged out so much, and the only sound was a thick Aussie accent yelling “NO!” he exclaimed, followed by “You’ve got be kidding me, love!  You and Huntz aren’t having sex!?” he exclaimed with a huge grin plastered across his face.

  
I nodded in slight agreement. “Well...then if that’s true love…please enlighten me as to how in the hell those sounds are coming from his room when we know you’re the one in there with him!?”

  
“What, Finn? Never made a girl scream just by using your mouth before?” I asked.  I had to admit, I was kind of proud to say it and just waited with a smirk on my face, for the implication to dawn on him.  

After what felt like forever, but was really only 30 seconds, Finn turned to face me - trying hard to make eye contact with me - though I was doing my best to avoid him. He cleared his throat and again placed a hand on my knee and opened his mouth to speak.

  
“Rory, Love, if you and Logan have been dancing around each other this whole time, and you’re doing everything BUT having sex, may I be so bold as to ask why you two aren’t just having sex?”

I hemmed and hawed, trying to think of a logical answer that wasn't coming out and telling him the truth.  Almost as if he could see my discomfort, Finn went on to say: “I’m pretty sure Logan has all the working parts, given his reputation; you and Logan are both hot for each other, right?  So unless your real name is Roger and you’re just waiting for the surgery then I don’t understand...”


	5. Chapter 5

**Summary for the Chapter:**

> Rory explains to Finn why it's not as easy as he thinks to just sleep with Logan. Let's see Finn's reaction to the big news.

**Notes for the Chapter:**

> I apologize again for those that have read all the way through, but I re-wrote this chapter as well and it has bumped stuff into the next chapter. I hate the thought of deleting it all instead of just copy-pasting over the existing parts.
> 
> I appreciate everyone who has read this and the few that have given Kudos! enjoy!

I was surprised that Finn hadn’t put two and two together yet. I took a few breaths to compose myself before speaking “Umm Finn, see the thing is, that well…” I stuttered trying to find the right words. Sensing my nervousness Finn looked at me “ Love, what is it, what are you trying to say?” he asked cautiously. I reached over and took a long drink of Finn’s spiked coffee “It’s a little more complicated than having all the working parts...” I trailed off, and then before I could stop myself the words poured out of my mouth, barely coherent and at lightning speed. “IMAVIRGIN! Finn that’s why, and Logan doesn’t know, and I know if I tell him he won’t understand, and he definitely won’t stick around to be someone’s ‘cherry popper’! He’s got a million girls on standby, he doesn’t need me. I just have so much fun being around him, and he makes me feel good, like no one else before, and I don’t want that to end!”

And exhale…

I was wringing my hands, waiting for Finn to say something, to laugh at me, to make some snide comment laced with an innuendo, but he didn’t.

He took a deep breath and let it out like he was in some yoga instruction video. I was looking at the ground, but I could feel Finn’s eyes boring a hole into my skull. When I was finally brave enough to look up at him, he had what can only be described as a compassionate smile on his face.

He leaned over and placed his hands on my shoulder, and then pulled me into a tight hug. He pushed a strand of hair behind my ear and whispered: “It’ll be ok, Love.”

I pulled back, searching his face for more details; more answers. I shook my head. “No, it won’t” I looked up to his eyes. “I need to break it off with him, don’t I? He’s never going to stick around if I tell him, will he?” I questioned shakily.

Finn looked at me sadly. “Here’s the thing, Love; I don’t want to agree with you but you need to know something about our dear friend Logan. When we were in high school he was much less cynical and jaded than he is now and he, in fact, could care less if it was a girl’s first time or not. He was always a gentleman and he’s never led a girl on to think that it was more than what it was and if it was 3 years ago I’d be telling you to go on and tell him and there wouldn’t be a problem. But our senior year of high school he met this girl Lacey she was sweet and kind of naive and she thought that Logan being her first meant that they were bonded together forever.

The next day she texted him upwards of 20 times, asking when she would see him again and why had he run out so quickly afterward. He just avoided her messages and went about his day until that night when he came back to his room and found her waiting outside the boy's dormitory and she demanded that he speak to her. He tried to explain that he was sorry she misunderstood his intentions but on no uncertain terms was he looking for a girlfriend. And he just walked away leaving her on the steps. He thought that was the last he would see of her but the next day she turned up at his favorite coffee shop and when he went to the counter to order she jumped in and ordered for him; exactly what he would normally order...it freaked him out and he hightailed it out of there.

Then a few days later we had a long weekend so Logan, myself, Colin and a few others went to Martha’s Vineyard for a few days. No one knew we were going but somehow Lacey ends up staying at a “friend’s” place just next door. To this day we still don’t know how she managed that.

Anyway, to make a long story short, that was the last time Logan slept with a first-timer. He avoids clingers at all costs now. Now I’m not saying you’re the clingy type but it tends to go with the territory.”

So, all that to say; if you tell him you’re a virgin, that will probably be the last you see of him. I hate to be harsh, but you know I’m not one to sugarcoat. Even though he does really like you, I don’t think he wants to take a chance on going through a stalker situation again .”

I felt so discouraged. “So what do I do, Finn? Just accept that’s the way things are and walk away?”

Finn just laughed. “Or you could always give it up to someone else first, someone who’s not scared of the big V… and then Huntz would never be the wiser” he continued, almost giggling to himself…but I wasn’t laughing.

I slapped my hand down on my knee “That’s it! I just have to find someone to get the job done and then Logan and I can finally move forward. Okay, now I just have to figure out where to find a willing candidate” I said, already pondering locations to scout.

Finn looked at me, astonished at what he was hearing. “Love, before you go propositioning all of the eligible males across campus, can I ask why it’s so important for you to be with Logan? I mean if he’s not the kind of guy you need...in your situation, and I mean that with the utmost respect...it’s just, why would you go through the hassle, to begin with?”

He had struck a chord, and I suddenly felt tears in my eyes. I explained that Logan was the first guy to ever treat me like I wasn’t precious cargo, he didn’t coddle me and he liked to push the limits. He was like a breath of fresh air in safe and predictable life. He made me more adventurous, he encouraged me and made me want to be a better writer and to want more out of life.

Finn sat there listening to every last word. When he realized I was done speaking, he looked at me seriously and sweetly at the same time and asked cautiously.

“Love, what would you think if I was the one to ‘get the job done’?”

I almost laughed, but stifled it, and instead questioned with a surprised, “WHAT!? Finn, you can’t be serious! You’re joking, right?”

He just replied plainly, “I’m not joking, and I’ll try to not be offended by your reaction” he grinned. “We’re friends, right? I care about you, and your first time should at least be with someone who cares about you - even if you're not in love. Besides, you know, without a doubt, that I’ll make it good for you” he finished with a wink and a devilish grin.  
  
Well… I’ve gotta say… I didn’t see that coming, but I wasn’t completely appalled at the idea either. I had so many thoughts going through my head like “how?”

“What was that Love? did you say something?” Finn asked me. I didn’t even know I had said that out loud. I was worrying my lip trying to collect my thoughts, but Finn just gave me a concerned look. All I could think was I didn’t want this to ruin mine and Finn’s friendship.

“How, how can we do this and not ruin our friendship, because the thing is we are good friends and I don’t want to lose that by crossing a line we maybe can’t come back from”

I had more to say but I was struggling to find the right words. I cleared my throat and pondered what I was about to agree to. The bonus of Finn being my friend was that I trusted him and he’s never given me any reason to doubt that he cares about me. It does make a lot more sense for it to be Finn than just some random guy I don’t know. I would still be having sex with someone who I wasn’t in a serious relationship with, I thought to myself… but I was ok with that.

“Finn this is a very generous offer don’t get me wrong but I don’t want to be a nuisance to you. I mean, I know you could have any girl you want so I know it’s not like you’re just looking for an easy lay… but I don’t want it to be a chore for you either. There are so many factors to take into account...this could get very awkward and what if Logan found out. Oh, my God, Logan can never find out!” I exclaimed. I took a deep breath making sure I had covered everything and it came to me, “Oh and Finn this might sound weird but like, how would we go about this… you know the semantics” I said slightly embarrassed.

Finn leaned over and put an arm around my shoulder. “Love let’s get a few things straight. First of all, sex is not a chore, at least not in my books,” he said winking at me “And you could never be a nuisance, you’re my friend and I’m helping you out, ok. Lastly, do you think I have a death wish…? Why on earth would I ever tell Logan this?” he chuckled. Pausing to think for a second, he then continued “and to answer how we go about it… I’m thinking about a 5-star hotel, lavish setting, room service, spa, the whole works. We’ll make a day of it, and then get down to the business of you getting rid of that pesky v-card.” He laughed, trying to put me at ease.

Listening to Finn describe his plan to “seduce” me, I couldn’t help think that it sounded like something you would do for a girlfriend. Finn didn’t strike me as the romantic type and he came up with that awfully fast, it sounded so thoughtful and personal it made me wonder if he had ever thought about this before tonight. Maybe he had intended it for Rosemary but when she turned him down for the hundredth time he just put it on the back burner… yeah, that had to be it I reasoned to myself.

As I was caught up in my thoughts he turned me to face him and continued, “Don’t freak out just yet, Love. We’re not doing it tonight or anything, so you can relax. Go make those lists you’re so fond of, think it over, and let me know… I’ll be waiting for your signal.”

With that, he placed a kiss on my forehead, grabbed his books and left.


	6. Chapter 6

**Notes for the Chapter:**

> Sorry for the long wait on this. My beta and I are both crazy busy so it's been slow going lately. Hope this tides you over until I can get more posted.

It took me a good couple of days to mull over Finn’s proposal. Lucky for me, Logan was out of town with his dad for the week meeting prospective clients. You know Mitchum, always chomping at the bit to get his son involved in the family business as soon as possible. 

I was kind of relieved that Logan wasn’t around, it made the thinking process a heck of a lot easier. So after weighing the pros and cons of Finn’s proposal, I decided that given the fact that he was a good friend, seemed to care about me and he definitely had experience that I really couldn’t go wrong with having Finn be my first. I was going to call Finn, and have him set it all up for Friday night. 

Grandma had advised us that they had a function to attend and so Friday night dinner was canceled this week. Of course, mom was appalled that I was ditching her and a Gilmore movie marathon for “friends”, but I had to do this, and I only had so much time.

I spoke to Finn on Monday to set it up and we hashed out a few details and he could tell I was freaking out. 

“Love, are you sure you want to do this? I mean you’ve waited this long for a reason are you sure you don’t want to just keep waiting. I don’t want you to feel pressured because I suggested this. You can think about it more if you want” Finn said reassuringly.

“I don’t feel pressured Finn, but your hesitation is making me think maybe you’re changing your mind,” I asked suspiciously.

“I’m not changing my mind, I just want you to be sure that’s all” Finn replied.

“I am sure Finn, and I want to thank you for being so great about all of this, but I do still want to go ahead with the plan…it’s just hard. I have so many things going through my head, and I don’t really have anyone to talk to… My mom’s out of the question, too much judgment there. Lane isn’t a good choice, seeing as she has even less experience than I do. And Paris, well… Paris is too clinical and truthfully too blunt and honest for what I need right now, if I wanted a lecture, well I’d go to my mom.” I sighed trying to release some of my stress. 

“If it’s just someone to talk to that you need in order for you to be 100% sure, then I might have a solution,” Finn replied, “will you be at your place this afternoon?” 

“Yes, why?” I asked cautiously, wondering where this was leading. 

“Don’t worry, Love. Just when someone knocks on your door, answer it.” I was still unsure but I agreed and we finished our call.

Around 3:00 there was a knock at my door, per my instructions I answered it. I don’t know who I expected to see but it wasn’t who I thought, it was Stephanie.

“Hey Steph, it’s good to see you, what are you doing here?” I greeted. 

“Geez, Ror! Is that any way to welcome your soon-to-be best friend?” she exclaimed with a laugh, as she pushed through the doorway past me and into the common room. 

I looked at her quizzically. “What do you mean ‘soon-to-be’? What’s going to change so drastically that it would put you in my top spot?” I joked.

“Well, a little birdie told me that you could use some help getting ready for a very important night and that well... basically, you needed a girlfriend to freak out with” Steph stated. 

I was shocked and apparently, it showed because before I could say anything Steph continued, “Now don’t freak out, Rory. Don’t be mad at Finn, okay? He was just trying to help, and the poor thing doesn’t match wits very well with the likes of me. But, then again, I did threaten to tell the entire female population at Yale that he had chlamydia. Poor boy didn't have a chance” she smiled proudly. 

Yes, of course, I was pissed at Finn that he would just broadcast my personal business! But, I’d also seen Steph withhold sex from Colin for weeks on end because she didn’t get her way, so I knew she was a force to be reckoned with. 

“I can’t believe he told you! I don’t know why I ever thought this was a good idea…” I ranted but was interrupted by Steph mid-sentence “Whoa! Ror, slow down. Wow! Finn said you were freaking out but I didn’t expect you to hit me with it so soon. I wasn’t prepared for that. Here, open this and get some glasses. If you’re this freaked now, we’re definitely going to need it” she said as she proffered a bottle of champagne from her purse handing it to me.

I walked into the kitchen, opened the bottle, poured two glasses and sat back down on the couch next to Steph.

She looked at me kindly. “Okay, hun. First of all, nothing goes past these four walls. I am a vault of secrets that will never see the light of day, so you can tell me anything. Now, Finn told me that you’re a virgin, though, with that body and those brains I’m stunned, that’s beside the point. He also told me you haven’t told Logan and while I understand why I mean the guy has a million girls on speed dial, so why would he stick around for someone with no experience, right? But it doesn’t negate the fact you haven’t been honest with him, which is strange. I kind of expected more from you” she said. 

I looked down, ashamed. I really hadn’t been honest with him at all. How could I expect him to commit and want to be with just me if I wasn’t truly committing to him?

Steph just reached out and touched my shoulder. “Ror, hun, don’t beat yourself up, okay? I get it! Finn gets it! Which is why he’s being such a stand-up guy and offering to do this huge thing for you… without you even asking, might I add. Sheesh, if I didn’t know better, I’d say the boy had it bad for you or something” She said with a laugh, slapping her knee. 

‘What did she just say? Could Finn possibly have feelings for me’ I thought to myself.

When she regained her composure, she continued, “But who are we kidding? This is Finn we’re talking about. The only thing he has feelings for is his dad’s collection of vintage scotch!” We both laughed at the thought of Finn walking down the aisle with a bottle of Macallan.

After lightening the mood a bit, we got back down to the topic at hand. “So you have to tell me how this came about… it's hard to wrap my head around, I mean, you and Logan have been cozy for a while now. How come the topic hasn't come up yet?” Steph asked. 

“Well, as we both know, Logan would freak out if he knew I was a virgin - and I would probably never see him again. So I’ve managed to keep his attention with “other things.” It’s not ideal, but it works for now, at least. It's like I told Finn - the relationship I have with Logan isn't like any relationship I've had before, he makes me feel things I never knew I could. And while all of that is true, Finn did bring up a good point - that if Logan isn't the kind of guy I can trust with something like my virginity, then is he even really worth my time and for now I'm willing to say yes. I still want to see where things could go with him. Does that sound crazy?” I asked halfheartedly.

Steph looked at me suspiciously, like she was trying to read my thoughts. “What do you want me to tell you, Ror? I don’t think it’s weird you want to give him your time, you guys are freakishly cute together and I’ve never seen Logan so ga-ga over someone in... well... forever. I say go through with your plan with Finn, you’ll be free of your v-card, and nobody else ever has to know.”

I pondered what Steph had just said. “So you don’t think it’s weird that my first time is going to be with my so-called boyfriend’s best friend? How is this going to work afterward? Will Finn and I still be friends? Is he going to look at me funny everytime he sees me? Arrrgh! I have so many questions!” I said with a sigh. 

Steph just rubbed my arm to calm me down. “Look at it this way - you are going to be sleeping with one of my best friends who is known to be quite the stallion in bed. Then, you guys will leave your little love nest and return to normal life. After that, you get to have sex with the only guy I know who has an even higher reputation in the bedroom than the aforementioned stallion. You can’t go wrong, sweetie! You’re living the dream of every girl on this campus. And on top of that, Finn is a total sweetheart, especially to the people he cares about. He’s not going to treat you like crap the next morning or look the other way when he sees you. Things will go back to normal as long as you let them. Although, that might be hard to do since this will be your first time and we females do tend to get attached… but just remember the goal is Logan, and you’ll be fine! I guarantee!” she declared with a peppy tone.

I nodded slightly to myself.

“So that reminds me, Finn kind of let me in on his plans for Friday and firstly I think you’re gonna love it. Secondly, I think you’re going to need something a little sexy and flirty to wear” Steph said, her eyes sparkling with excitement. 

“What!? No way Steph, no way! Look at me! Do I strike you as the lingerie type of girl!? And honestly, how can I be flirty and sexy with Finn when we’re not together? We’re friends! I can barely get over the fact that he’s going to see me partially, if not fully, naked!!” I exclaimed

“Come on, Ror! We both know Finn is a fully sexually-functioning 20 something-year-old guy, but you gotta throw the guy a bone. It’s going to be weird for him, too, don’t you think? I mean, you guys are pretty good friends and Logan is his best friend... He’s sacrificing himself for yours and Logan’s tentative relationship, this is gonna be a little awkward for him at best. He’s going to need a little something to get the fire started if you know what I mean” she hinted with a wink.

I thought about it for a minute and it actually made some sense. “You know Steph, I hadn’t thought about it that way, but you have a point” I reconciled. “Would you come shopping with me? I’m not good at this stuff, and I would have absolutely no idea where to start” I asked as panic started to rise.

Putting her arm around me. “Of course I’ll come shopping, I couldn’t leave you to your own devices! We don’t want you showing up in Fruit of Loom, now do we?” Steph teased. I just rolled my eyes at her. “Well this has been a trip, Ror, I’m glad I could put your mind at ease, but I’ve got to go. Colin and I have plans tonight. How does Wednesday afternoon sound for shopping? I’ll pick you up here around noon?” She asked. 

I nodded. “Sure, yeah, okay. Wednesday sounds good.”

We gave each other a light hug. I thanked her for her help, and walked her to the door, letting her out.


	7. Chapter 7

I spent the rest of Monday and all day Tuesday a fidgety mess. I was excited but nervous all at the same time. Both days were spent with possible scenarios of what was to come running through my head; everything from the niggling fear of the unknown and the awkwardness that could follow to the nitty gritty intimate details of what I was about to do. Thankfully Wednesday was filled with the distraction I so needed that only Steph could provide. 

We spent the day shopping as scheduled; first stop, Victoria’s Secret. I wasn’t looking forward to this as I hate bra shopping, to begin with, but after what Steph said the other day I didn’t feel like I had much choice.

“Okay Rory, so what size are you like a 4? God I don’t know how you can eat like you do and stay that thin” Steph said as she started perusing racks of lingerie. “It’s the Gilmore genes I tell you” I stated proudly. “Oooh Ror come check this out, this blue would look amazing on you”, I stared at Stephanie in shock as she held up a very sheer, very skimpy blue lace teddy. “Steph there is barely anything there to wear, it’s not like Finn’s my boyfriend and I’m putting on a sexy fashion show for him. Whatever I buy has to serve two purposes: be sexy enough to get Finn in the mood and be comfortable enough so that I’m not pulling and tugging at it all night. I replied exasperated.

“Well look at it this way if you get this Finn won’t be able to keep his hands off you so you won’t be wearing it for long,” she said firmly trying to convince me to see things her way. “It’s not happening Steph, let’s just put that back over there nice and easy,” I say calmly, trying to keep her placated as I placed the garment back on the rack.

“Ok well if you’re not into sheer and sexy what about this, it’s not sheer and it’ll push up your boobs nice and high!” “I don’t think so Steph I’m not a medieval bar wench so I’m going to say no” and I took the ivory corset from her and just placed it back where she found it.

“Alright well I give up...what is it you want then?” she asked sounding frustrated.

I sifted through the racks a bit more looking for something to pop out at me, I picked up a really pretty baby blue lace teddy that Logan would probably love, he always compliments me when I wear blue. As I contemplated buying it I remembered why I was here and what Steph had said, this was for Finn and she was right I needed to get something that would make sure Finn did not have any second thoughts and so I had to find something that was going to blow him away. I placed the item back on the rack and shook all thoughts of Logan out of my head. I walked towards the back of the store where the new collection was and right before my eyes I spotted the most amazing red satin babydoll set. It had a plunging neckline and showed off my midriff and had a matching thong to go with it. This was perfect!

I called Steph over to show her “Look Steph, I found it!” I said happily. “Where, which one?” she asked. I held up the one I had found and her response was unexpected “Are you sure Rory?” “Absolutely sure! It’s perfect, the red is sexy, and the low cut neckline is sure to get any guy’s motor going so I don’t see the problem. I think Finn is going to love it” I replied enthusiastically. This actually hadn’t been as dreadful an experience as I thought it would be I thought and proudly made my way to the cash register.

After shopping, we went to a nearby cafe for lunch,we sat down with our sandwiches and coffee, Steph promptly pulled out her phone and started texting one of her friends, while I waited for her I took out my copy of ‘Leaves of Grass’ and started reading.

After what felt like a few minutes but turned out to be half an hour Steph looked up from her phone after noticing the time she nudged my elbow off the table making me drop my book on the floor. “What was that for Steph,” I asked rather curtly. She just looked at me somewhat annoyed “you’d better hurry up and eat if you’re going to make your appointment next door” she said smiling. I was confused “What appointment? I’m not getting anything waxed” I replied thinking I had shut her down. “Au contraire mon amie” Steph responded confidently. “Steph, I don’t need a wax I just shaved my legs last night,” I said. “I’m not talking about your legs Ror,” Steph said and then waggled her eyes downward.

“NO!” I nearly shout. “Rory, now be a good little girl and go next door,” Steph replied confidently like a parent whose child just did what they were told, and she picked her phone back up and took a sip of her coffee before waving me away with her hand.

I knew it was a losing battle so I picked up my purse and reluctantly walked into the salon and gave them my name. “Oh, yes, Ms. Gilmore, please come with me.” I followed the woman to the private room near the back. “I’m, Katrina. Now, I’ve got you down for a bikini wax, but I’ve just had a cancellation and I could do a full Brazilian if you’d rather.” 

I think I turned fifty shades of red at that moment. But if I was going to do this thing I was going to do it right so I sucked it up and let her get to work. How bad could it be if women do this all the time?

After that traumatizing event, I was worried I wouldn’t be able to walk, let alone have sex. I couldn’t help but think “how do women actually do this on a regular basis?”

I went back to the café next door to find Steph sipping on a mimosa. She was flipping through a magazine and had a smile on her face that was a mixture of joy and mischief. “What did you get up to while I was gone,” I asked suspiciously as I attempted to sit down. “Not much, just reading my magazine, what’s with you? You have a weird look on your face” she said curiously.

“Well, it turns out Katrina had time to do a full Brazilian so….” I paused and then whispered “ I can barely walk now Steph” in a huff. “Oh, don’t be so melodramatic.” She replied as she rummaged around in her purse and pulled out a container with some brown pills. She handed a couple to me. “Here, take these and you’ll be as good as new. “I’m not taking some random pills from a sketchy tin in your purse” “Ror, it’s just ibuprofen. It will help with the pain and discomfort.” she reassured me. “Oh, ok,” I said and swallowed the pills down with some water.

“Alright I think you’ve had enough fun for one day, let’s get you back home before your roommate thinks I’ve kidnapped you.”

We arrived back at my dorm 30 minutes later, I opened the door and found Paris standing there with arms crossed looking rather irritated. As I crossed the threshold she pounced “ Gilmore where have you been? You usually come back here after class” she questioned. “I went shopping with Steph, what’s the big deal” I replied as I walked past her to go to my room.

“You’re walking awfully funny for someone who just went shopping! Oh, no, don’t tell me you gave it up to that waste of a trust fund Huntzberger.” I couldn’t help but blush, not because she was right but because it was far more embarrassing than that. “You did! Rory, I can’t believe…” She started to say before I interrupted. “No, Paris, I didn’t have sex with Logan. I got a bikini wax, ok?!” I replied bluntly. “You’ve never had one before? What possessed you to do something like that?” she asked. Before I could answer she continued. “ Did Huntzberger say something? Where’s your inner feminist Rory, you’ve got to stand your ground on things like this if he can get you to cave on this who knows what else he can convince you to do!” she ranted.

I couldn’t handle Paris’ crazy right now so I just held up my hand in surrender, and swiftly walked into my room and closed the door behind me.


	8. 8

**Notes for the Chapter:**

> I apologize profusely for the long wait. These next few chapters had been posted on other websites and somehow I forgot to post here. Oh, well at least now you'll have a feast to tide you over until I can continue.

On Thursday morning I slept in a bit as I didn't have a class until 11. When I got up I decided maybe I should start packing. I grabbed a cup of coffee and some pop tarts and headed back to my room and started planning out what I would need to bring with me. Over the phone Finn had mentioned a spa so I made sure to bring a bathing suit and some comfy sweats to put on in the hotel room, a pair of jeans and a t-shirt for Saturday, an outfit for dinner on Friday and last but not least my sexy red lingerie.

I looked through my shopping bag from the lingerie store so I could wash it out before packing and noticed it was not in the bag. I searched my room from head to toe and couldn't find it anywhere. I started to panic a bit but I didn't have time for that now, I had class in 45 minutes and I still needed to shower and get myself ready so it would have to wait until later.

On my way to class, I texted Steph to see if maybe she had it in her bag by chance, but she hadn't seen it. So I made my way to class and decided to deal with this later.

When I returned to my dorm after class there was a gift-wrapped box at my doorstep with a note addressed to me. I picked it up and brought it inside to open. I threw my book bag and jacket on the couch and started ripping away at the paper, I couldn't possibly think what could be in there.

When I opened the box I was surprised to see pretty pink tissue paper, and when I peeled it away I found a beautiful teal satin negligee that had a black lace border around the edges. It was gorgeous, to say the least. When I rummaged through the box and wrapping to see if there was a card to show who it was from I came up empty-handed, except for a little note that said "Wear Me" on it. I assumed it was from Steph as she didn't seem too pleased with my choice yesterday, but what if it was Finn I wouldn't want to make anyone feel bad by getting it wrong so I let it go. I would find out soon enough.

I had a pretty laid back day ahead of me, some studying and homework and an assignment for the paper, but aside from that I pretty much just finished packing my bag, showered and got an early night so I would be prepared for the next day.

Friday came around like it does every week, and I could barely keep my food down. I was overdosing on coffee, trying to settle my nerves - yes it works for some people as addicted to coffee as me.

I kept double checking that I hadn't forgotten anything. Thank God I only had one class in the morning because I was barely able to concentrate; I still have no clue what the professor was talking about.

It was noon when Finn showed up at my door. I let him in and continued running around in a frenzy trying to get my stuff together. Suddenly Finn just reached out and lightly held my hand in his and looked down into my eyes "Rory, you're still sure you want to do this right?" he asked. I looked back at him and nodded my head in assent. Finn then automatically picked up my overnight bag, as well as my book bag and purse, and with a slight nod of his head said "C'mon love, let's go make you a woman," with a wink and I couldn't help but giggle at his words.

I was actually surprised at myself that I didn't back out and tell him to just leave. I just had the overwhelming sense that I needed to do this.

When we got downstairs a limo was waiting for us 'he really did go all out' I thought to myself. Once we were in the car, he could see the nervousness on my face and the way I was fidgeting. He took my hand in his and told me everything would be fine, and he reminded me that I could call it off anytime I wanted. He actually put me at ease with his quiet demeanor and gentle words… Most people think Finn couldn't be anything less than abrasive, but they haven't seen this side of him.

Once I'd stopped fidgeting, Finn offered me some champagne. I gladly accepted and drank it a little too quickly. We began chatting about movies and music and I was so absorbed in our conversation that I had unknowingly moved over a significant amount from where I started and was resting my hand on his leg.

I couldn't believe how relaxed Finn and the champagne had made me. I felt a bit self-conscious now and deep down all I could think was "am I flirting with Finn, my actions would say yes but I hadn't meant to put my hand on his leg" and then I thought "he must be feeling so awkward, he's being so nice, and the only reason he's not moving my hand away is because he doesn't want to hurt my feelings", so I slowly started to pull my hand away but Finn just moved his over mine again and patted it twice. I wasn't sure if he wanted me to keep my hand there or not so I looked up at him for reassurance, he just smiled sweetly and I relaxed back into my seat and enjoyed the rest of the drive.

We drove about 30 mins and arrived at the Madison Beach hotel. I was in awe just seeing the exterior; I could only imagine the inside. This place was beautiful with a classic, seaside resort-look with just a hint of elegance. We got checked in and they had our luggage taken up to our room.

As we stepped into the room I gasped at the beautiful setting before me. It wasn't over-the-top or ostentatious, but just really elegant and had a breathtaking view of the beach. There was even a little balcony for us to enjoy our morning coffee on. Wow, even if everything else went to hell, I would really enjoy staying here for a night.

In the end, I think Finn was really trying to make me feel comfortable, and he knew anything too extravagant would do the exact opposite.

As the bellboy left and the door closed behind him, Finn came over and put his arm around my shoulder "Love why don't you take it easy for a bit, maybe curl up on the bed with a book. I know you have one in your bag at all times and since you have 3 bags I'm guessing you won't have a problem finding something to read," he suggested.

I walked over to my bags to find a book as Finn continued speaking "I'm going to order us some lunch, I'm starved and I'm figuring you are too since you had an early class. What do you want to eat?: he asked. "What about a mix of things, I don't want anything too heavy, but make sure there are fries, that's all " and I gave him a flirtatious smile. "Of course fries for Miss Gilmore", Finn replied sarcastically.

After ordering the food Finn took he out his laptop and started working on a paper he had due for class. Before I knew it, I was swept away in my book. We just sat there in companionable silence, each doing our own thing. It gave me a weird feeling like it was a very couple-y thing to do.

Lunch came and we had an assortment of appetizers, fries and onion rings. Finn had ordered a bottle of wine and some beer to go with it "Pick your poison Love," Finn said holding up a bottle of each for me to choose from. When he saw how uncertain I was he walked over to the mini bar in the room and came back holding a Sprite and a Coke "or maybe you'd prefer a soda" he inquired with an understanding look on his face. I took the coke from his hand and we dug into our food.

After lunch, Finn told me to go change as he had booked a massage as well as a mani-pedi for me and advised me to bring my clothes for dinner as he would meet me at the spa afterward.

After all the tension and stress had been worked out of my body and I was finally feeling like myself again it was 6:00. Before leaving the spa I had changed into my skirt and blouse, I had a blazer and boots with it and my teal satin negligee underneath. Despite it being mid-May, it was still pretty chilly out.

I met up with Finn in the lobby, and he had his arm outstretched to greet me with a hug. "Did you have a nice time, Love? I hope it got all those knots and kinks out" he says sweetly.

"It was amazing, Finn! I feel so relaxed! Having said that as much as I would love to lie down and go to sleep right now, I am famished. Shall we go eat?" I ask as I hear my stomach start to growl.

"Of course, Love. I know better than to keep a Gilmore girl from her food" he said and we made our way to dinner.

We arrived at the Wharf restaurant attached to the hotel. As we enter, I am truly amazed at the beautiful decor of the restaurant. It was nautical inspired, but not in a kitschy, cliche kind of way. This was classic blue carpeting and seating with white wainscoting to offset it. I felt like I was on a cruise ship, except not as gaudy.

The restaurant's reputation precedes itself and I was really excited to try their baked stuffed shrimp as I had heard rave reviews.

Again, Finn took it upon himself to order a bottle of wine, which I definitely appreciated since, despite my best efforts, my nerves were still wreaking havoc.

All throughout dinner, we talked about school and the next LDB events coming up. As we talked and laughed, Finn continuously rubbed his thumb over my hand, helping me feel more at ease.

When the dessert menu was placed in front of us, my eyes widened at the sight of 'molten lava cake', and I felt like a three-year-old begging their parents to let them have candy before bed. "Oh C'mon, Finn! It looks so good, how can you say no to all that ooey-gooey goodness!?" I whined as I gave him my best Bambi-eyed pout.

Finn laughed but suggested maybe we might want to wait for dessert until later. "Love, we can order dessert up to the room afterward, we don't want you feeling ill now do we?" he asked with a wink. That was enough to convince me.


	9. 9

**Notes for the Chapter:**

> It's going to get a little steamy in here, hope you're prepared!!

We had the waiter add the charges to our room bill. Finn helped me put my jacket on, then he took my hand and we walked outside to the beach. It was getting pretty cold and Finn put his arm around me and guided me over to a bench just on the sand. The sun was mostly set at this point, but you could still see and hear the waves coming in… It was nice.

After a few moments of silence, Finn placed his hand on my cheek and turned my head to face him and spoke softly, “You know, when I planned thing whole thing I might have overlooked one tiny detail” he said. “Oh,” I prompted… “What if you don’t like kissing me?” he asked with a smirk. 

I laughed lightly but nodded as panic started to set in. “Oh my God you’re right! What if we don’t have any chemistry at all!? What if you don’t like kissing me, or maybe you know you're not attracted to me… Oh god, and you went to all this trouble…” I rambled. 

Then suddenly I was cut off by Finn placing his hand gently behind my head, pulling me in and kissing me softly, but soundly at the same time. My eyes fluttered shut. I placed my hand on his forearm that was supporting me, angling my head so we could deepen the kiss, and I let his tongue enter to dance around with mine. I know I was supposed to be freezing, sitting on the Atlantic coast in May after the sun has gone down, but there was a warmth running through me that felt like hot cocoa on a snowy day. 

I couldn’t break away, and it was only when my other hand made its way to the back of Finn’s neck, that he shuddered from the chill and broke away giggling. “Well we definitely know there’s chemistry, but let’s get you inside before you get hypothermia,” he said smiling. He took my hand and I snuggled into his side and we walked back towards the hotel.

On the elevator ride up, Finn kept me close to him, his arm draped over my shoulder. Any onlookers would have probably assumed we were a couple and oddly, the thought didn’t make me embarrassed or self-conscious in the slightest. 

When we got to our room, Finn swiped the card and ushered me in ahead of him, so I was first to see the most amazing, romantic setup you could ever imagine. It was like something out of a movie.

I gasped at the sight of all the candles and flowers displayed around the room; even the fireplace was lit, adding that little extra ambiance. I’m sure I looked crazy, but I was filled with wonder and sincerely touched that someone would go to these lengths, just for me.

I turned to face Finn and I’m pretty sure he freaked seeing the tears starting to form in my eyes. It was my turn to assuage his fears. I just leaned up on my tiptoes, kissed him sweetly on the lips, and whispered: “thank you”.

He leaned down close to my level, placed his hands on my hips, and continued the kiss for a few more moments. When we pulled back, he looked me in the eyes with such care and emotion, that I just about melted.

Since when was Finn such a romantic?

He took my hand and led me over to the fireplace so we could warm ourselves up a bit. Leaving my side for a moment he went to retrieve the champagne and glasses that had been set up on a table across the room. 

In the meantime, I removed my blazer and boots placing them nearby. 

Finn returned with two glasses of champagne and offered one to me. He turned to face me and said “I think a toast is in order, Love, don’t you?” he proclaimed. He paused to think for a moment, and then continued. “To new adventures. ”

I laughed and then added, “and to REALLY good friends.” We both laughed, though Finn’s response seemed a little vacant. I decided not to press the issue so we clinked glasses, and then drank our champagne.

Finn took our glasses and placed them on the side table, and then he looked at me genuinely and said, “You know, Love, I really wanted to do this to help you out, but I can’t deny I’m really enjoying myself… And we haven’t even done anything yet” smirking as he spoke.

He then took my hand and led me over to the bed and we sat down next to each other. He placed his hand on my cheek, caressing softly with his thumb. I couldn’t help but notice a different look in his eyes; they were so clear and glistening.

I didn’t know what he was thinking, and before I could ask, he leaned down and kissed me softly. I reciprocated, and we stayed like that for a while, before we got lost in a passionate embrace.

Finn still had one hand on my cheek and the other placed firmly on my hip, I soon realized he was trying to pull me closer, but before I could think twice, I was pulling him up to the top of the bed with me, not so gracefully, and we collapsed; giggling, with Finn lying half on top of me.

We were face to face now. Finn had removed his hand from my waist briefly and tilted my chin up to look at him. “Are you okay, Love? Is this going too fast for you?” he asked sweetly. I simply placed my hand on his neck and pulled him down, kissing him thoroughly, hoping that was answer enough.

We had been kissing for a while when his hands started to roam. He pulled me onto my side and his hand traveled down my back lower and lower.

I felt as if he were holding back, his hands stopping at my waist. I wasn’t sure why he’d been afraid to go any lower, so I decided to give him some encouragement. “You don’t have to be scared, I won’t bite,” I whispered in his ear and I moved his hand lower. As soon as I did that it was like a beast had awoken inside of him. He moaned a deep, sexy growl and I felt the heat pool between my legs.

He pushed me gently onto my back and slowly slid his hand around my waist and then glided over my stomach, leaving a trail of fire in its wake.

Gauging my reaction and finding I was most definitely enjoying myself, he moved his hand up under my blouse and could feel the satin of my negligee underneath. 

He lightly traced the top of my breast where the lace border met my skin, immediately my nipples hardened, my back arched and my breath hitched at the sensation. The spike in passion sent my hands running through Finn’s hair, then down inside the collar of his shirt and grasping at the bronzed skin of his shoulders.

I was feeling more certain, and sure of myself so I sat up and started to undo the buttons on my blouse. Finn just held my gaze for a second then removing my hands from my shirt, he took them in his. Leaning forward he stared deep into my eyes and spoke in a soft tone “here, let me.” gently moving my hands away from the buttons.

His fingers set to freeing the buttons, and once again his mouth took possession of mine. He slid the shirt off my shoulders and threw it on the floor. His fingers grazing my shoulders lightly as he laid me back down.

With the top of my teal colored lingerie now revealed Finn looked down in adoration and I saw the pink rising in his cheeks. “Did you buy something new just for me?” He asked in a husky tone and I felt a bit self-conscious “do you like it” I asked sheepishly. Finn leaned in next to my ear and whispered “You’re making this way too easy for me Love,” with a hint of allurement in his voice. Before I could respond I felt Finn’s lips caress my neck just under my ear then nipping lightly down to my collarbone

As I tried to absorb the words Finn had just spoken and the meaning behind them, I felt Finn’s hand make its way up to my tender breasts, and he began to massage and caress them. I felt heat stir in my abdomen and I moaned at the pleasure I was feeling. I had gotten this far before with other guys, so I couldn’t make sense of why this time it felt so different... so delectable... so hot.

My hands were running up and down Finn’s back, now looking for some kind of purchase. The sensations he was causing with just his hands were driving me wild, and I couldn’t wait for his mouth to come down and worship my chest. 

As I moved my hands around to the front and over his chest and abs Finn pulled back, kneeling he pulled his sweater off over his head, revealing his tanned muscular physique. I reached up; wrapping my arms around his neck and pulled him back down where we collided in a fiery kiss.

We kissed for a while until I noticed Finn was running his fingers lightly along the straps on my negligee but not pulling them down; so I sat up and reached behind me to undo the clasp at the back of the garment to give him better access. Without me even asking, he just reached around and unhooked the clasp with skilled fingers and I felt it release. Finn’s hands came back up to my shoulders brushing them gently then pulling the straps down my arms as he laid me back down.

Finn looked down at me and my bare breasts were presenting themselves for the taking. We made eye contact and for a second it felt like he was trying to see into my soul. There was no hesitation when he leaned down and we met in a sensual kiss. 

Slowly Finn moved down to my neck and kissed his way to the swell of my breasts; he kissed and teased with his tongue making a trail to the valley between them. Eventually moving his head over; grazing them with his lips and sweeping his tongue over each nipple, before finally taking one into his mouth. He went back and forth between them, laving and sucking on one while massaging and caressing the other with his hand.

Soon I was writhing underneath him. Finn then suddenly slowed down and started placing kisses on my chest, and up to my collarbone, giving me a chance to catch my breath.

He pulled back and tucked a piece of hair behind my ear. “Do you want to keep going, Love? Are you comfortable?” he whispered, looking for assurance to continue.

“Yes, Finn, I’m comfortable. I trust you, and I definitely want to keep going” I replied.

Only at this point did I notice I wasn’t that nervous anymore.

Taking me at my word to keep going, Finn sat upright and started pulling the blankets down on the bed, I got off the bed to help out. When we had finished Finn came around to my side and placed his hands on my hips leaning down to capture my lips in a soft kiss. As the intensity of the kiss grew Finn reached down to the button on my skirt opening it with nimble fingers, while my hands traced patterns down his chest and abs.

As I reached the faint trail of hair below his navel I took a small breath and undid the buckle on his belt. Finn now had one hand on my back steadying me as he tugged my skirt down and it fell to the floor; the action propelling me to take the next step. I smiled up at Finn and then slowly pulled the zipper on his pants down and pushing them off of his hips and he stepped out of them as they fell around his feet. 

As I sat back down on the bed I couldn’t help but notice the massive erection Finn was sporting. I gasped slightly at the sight, and Finn just looked at me teasingly. “Don’t worry, Love, it looks a lot more ominous than it really is?” he said.

I blushed and we both laughed at what he had said.

Finn reached his hand out for me to take and he pulled me back up in front of him. Stroking my cheek gently with his knuckles he then started kissing me right under my ear again- a spot he figured out was one of my weaknesses. I placed my hands on his shoulders, scratching ever so slightly as I melted into the embrace. I felt his hand tracing lightly on my thigh, going higher and higher up with every stroke. 

He began lifting the hem of my nightie, sliding it up past my hips and then finally I lifted my arms so he could pull the garment off over my head. As he did so, he leaned down and whispered: “As much as this looks amazing on you, Love, it really needs to go.” 

I shivered at the seductiveness of his words.

We moved back to the bed and as I laid down I brought Finn down into a fierce kiss, nipping and sucking on his bottom lip. Finn’s hand was caressing down from my breast to my waist, and further still to the band on my black lace panties.

He now traced his finger along the lace that met the inside of my hip, so close to where I needed him to be. I felt tingles all over me, and slowly my brain shut off, and my body took over.

I wrapped my arms around Finn’s neck, pulling him down on top of me, needing to feel his warmth. As I lifted a leg over his hips, I could now feel his erection pressing rubbing against me.

Grinding against him as hard as possible, I was desperately craving the friction that only he could provide he groaned and pushed back with intensity, causing me to gasp and then let out a sultry moan.

Our kisses became even more frantic and I scratched my nails down his back. Oxygen became necessary, and we both pulled out of the kiss. 

Finn looked down at me, his eyes filled with desire. “Mmmm god Ror” he let out in a gravelly voice. His arms twitching slightly as he hovered above me “are you still sure about this?” he questioned. I took his head in my hands, cupping his cheeks. “I’m ready Finn,” I said assuredly.

I grabbed Finn’s arm pulling him back down on top of me and I purred into his ear “Please, Finn... I want you.”


	10. 10

**Summary for the Chapter:**

> We pick up where we left off. Will Rory go through with the plan to have Finn take her virginity... read and find out?

**Notes for the Chapter:**

> I apologize profusely for taking so long to post this chapter, hopefully, the last chapter was intriguing enough to keep you hanging on. Hope you guys have a fan handy cus this chapter is pretty hot if I do say so myself. NSFW (not suitable for work) it goes without saying. As always feedback is appreciated and enjoyed! Enjoy!

Previously

I grabbed Finn's arm pulling him back down on top of me and I purred into his ear "Please, Finn, I want you."

___________________________

Finn groaned in my ear then our mouths fused together with passion. As things became more intense he rolled off of me to the side, his hand boldly fondling my breasts while our legs intertwined and I angled my hips in such a way that I could feel the heat from his arousal between my legs. As we pulled out of the kiss Finn ran his tongue along the column of my neck and his hand moved down to cup me between my legs and then slowly started playing with the band on my black lace panties.

I was so engrossed in the moment that I didn't hesitate to lift my hips up and help him to pull them off, his hand caressing my ass as he went.

After doing so Finn came back up and laid next to me immediately kissing me again. My hands were running through his hair, and his hands were caressing every inch of my body.

As his fingers traced lower down my abdomen, I knew where he was headed and my breath hitched in anticipation.

He ran his index finger gently down my slit, in search of that hidden nub, and once he found it, I knew this would be the death of me. He delicately swirled his finger around a few times and my hips lifted up to meet him, he knew he had me and so he slowly delved one finger into my warmth. Shortly after he added a second finger and crooked them to find that special spot; it didn't take long before I was panting.

Pulling his mouth away Finn kissed along my jaw, as his thumb teasingly brushed my clit. When he applied just the right amount of pressure, I moaned loudly at his touch and grasped frantically at the sheets beneath me.

I was so wet at this point and it only increased as Finn started kissing around my navel and then lightly kissing his way lower. I couldn't believe what he was about to do but I didn't want him to stop.

He kissed his way up my thigh, I could feel his hot breath as he paused in the middle before kissing his way up the other side. He took my nub in his mouth, tracing his tongue around it, while his fingers continued working their magic. I felt myself getting close and he must have known too because he removed his fingers. Just as I was about to protest he brought his mouth back to my center delicately kissing my entrance a few times then I felt his tongue tracing me and before I knew it he was dipping it in to taste me.

I couldn't help the groan that came out of my mouth. As my back arched off the bed and my hands grasped tightly at Finn's hair he placed his hands on my hips to steady me. Stroking my core over and over with his tongue then dragging it up to tease the swollen nub and taking it into his hot wet mouth working me into a frenzy of need. His fingers returning to their position causing an inferno inside me. After one more bold caress of his tongue, my climax hit and I was drowning in waves of ecstasy, moans of pleasure escaped my mouth and I felt like I was flying.

Soon after, I felt Finn's presence above me, he whispered in my ear in a husky tone, "That wasn't so bad now was it?" and I could feel him smile against the side of my face.

It made my heart skip a bit, and my walls pulse around his fingers that were still firmly fixed inside me. It took a few moments before I released him, at which point Finn leaned over and kissed my forehead, pulling the sheet up over me as I came down from my high.

He laid next to me and ran his fingers through my hair bringing me back down slowly. As I rode out the final ripples I heard Finn rustling in a bag next to the bed, when I opened my eyes I saw he had placed 2 foil packets on the nightstand. "Two...? Wow somebody has high hopes" I teased.

Finn giggled, and I swear it was the cutest thing I've ever heard. "Don't worry, Love, I would never assume," he said with a wink, and then continued " I'm always prepared just like a boy scout," he replied simply.

As Finn was putting stuff back in his bag I couldn't help the thoughts that were sneaking back into my mind. I had talked about it with Steph and she had kind of helped put me at ease but I was still nervous. I had heard so many stories about the first time being painful I just hoped it wasn't as bad as I was imagining.

Finn climbed back up next to me and lightly ran his fingertips down my arm, causing goosebumps to appear. He leaned over and kissed me softly, soon his tongue teased my lips apart and the kiss became greedy and lust-filled. I ran my hands down his muscular back and lower to his perfectly sculpted ass. My actions taking him by surprise, he pushed against me and I could feel his erection pressing into my hip.

All I could think was, 'He must be in agony,' because we had been going at this for a while now.

Before I could stop myself, I reached my hand down and stroked him lightly through his boxer briefs and he groaned in appreciation. I can't lie it really turned me on.

Being able to get that kind of reaction out of Finn gave me so much confidence, so I pushed his boxers down to free him and I wrapped my hand firmly around his length. He groaned "Dear God woman, don't you dare move that hand. I may not be a teenager, but I might very well lose it all over those pretty little fingers of yours," he responded hoarsely.

I looked down to see Finn pushing his boxers off the rest of the way and a volcano of desire began to bubble up again.

Now free of all clothing barriers Finn returned to the top of the bed, pushing himself up on his hands so he was hovering over me. I could see the lust in his eyes, and I felt warm all over. He lowered himself a bit until our thighs were touching and whispered in my ear, "Are you ready, sweetheart? I don't think we can prolong this anymore."

"I'm definitely ready, I don't want to wait anymore" I replied, need apparent in my breathy tone. I began placing kisses along Finn's collarbone, he tilted his head back to give me better access and then brought it back down to look me in the eyes. He kissed me thoroughly and said "Okay then." turning the simplest words into the sexiest thing I've ever heard.

Finn reached over and grabbed a condom from the nightstand, I bit my lip as he rolled it on himself, unsure if he had expected my participation or not. Now that I could see his manhood - as my mom would say, in all its glory - I was suddenly nervous again and yet excited about what was still to come.

He must have seen the gears turning in my head because at that moment Finn leaned down to look me in the eyes, he spoke softly. "Ror, are you still nervous, Love?" he asked sweetly. "More about it hurting than anything else" I replied blushing and I turned my eyes away. He gently placed his hand on my cheek turning my face towards him and he looked at me with compassion "don't worry love I'll do my best to make it as painless as possible and it'll pass pretty quickly; but you can always dig your nails in if you need." he reassured me, then smiled sweetly.

I pulled his face down to me and kissed him eagerly. The heat returned almost immediately and I felt Finn reach down between us and tease that sensitive spot a bit with his thumb and I delighted in the reaction it evoked from my body.

Finding that I was still ready, Finn sat up, spreading my knees a bit further apart he moved between them. He caressed my legs for a few moments, helping me to relax. I looked up at him with a shy smile, and he returned the gesture, his eyes shining as he did; my mind and body contented at the action.

Finn leaned forward making eye contact with me "Ok, last chance Love, do you still want to do this?" Finn asked softly, as our bodies aligned. I brought my hand to his cheek stroking lightly "yes I do" I replied easily and I felt him enter me slowly.

I closed my eyes to keep myself centered, he stopped moving forward, and his hand came up to caress my cheek. I opened my eyes to look at him and despite the uncomfortable feeling between my legs, I felt completely at ease.

Giving me time to adjust Finn leaned down and kissed me firmly on the lips plucking and nipping leaving them swollen and a shade darker than before.

He moved his head down and placed kisses all over my breasts and finally sucking the peaks into his luscious mouth.

Soon I was writhing and moaning, the need becoming unbearable and that was when he covered my mouth with his and thrust into me with skilled effort.

I felt the pain throbbing between my legs, digging my nails in I let out a muffled scream.

There were tears starting to pool in my eyes that I didn't want Finn to see, but they started trickling out the corners of my closed eyes. I felt his hand gently wipe them away, then he leaned his head down and said tenderly, "I'm so sorry sweetheart, I didn't want to hurt you."

My eyes met his and I replied, "I know, Finn, it's ok. The pain is starting to go away already, I'll be fine, don't worry." I said appeasing his concern and I leaned up and kissed him with a smile on my face.

"If you're sure you're okay, then can we continue; it gets better I promise," he said reassuringly.

We were both grinning as our lips crashed into each other, then Finn reached down and pulled my legs up to wrap around his waist.

I felt him begin to move inside me and just like that, I was beginning to forget the pain I had been feeling mere moments before.

Slowly, Finn started grinding against me and then gently pulling out and sliding back in, setting a careful pace. It felt amazing but still very tame until his skill and experience became apparent when he hit a spot that I didn't even know existed.

I arched my back allowing him to plunge in even further. Reeling from the sensations; I placed hungry kisses along his throat and collarbone and over his taut shoulders, then tearing my mouth away from his skin I moaned, "Oh my God, Finn!" while my mind clouded over, and my breathing became erratic, my body tingling from the pleasure.

Taking that as a sign I was close, he then shifted one of my legs so it was over his shoulder, obtaining the perfect angle and that was the end of me - electricity radiated through me and the feeling of pure satisfaction coursed through my veins.

Amidst my comatose state, I could hear Finn let out a few moans of his own, then huffs of warm breath expelled against my ear as he found his release.

Still propped up on his elbows and sweat glistening on his forehead, Finn opened his eyes and looked at me with the utmost sincerity; he grinned at me and pushed the wet hair off my forehead.

Then, breaking the silence, "Darling, I would be content to just stay like this but I don't know how much longer I can hold myself up, so I kind of need you to remove your nails from my back if you could," he said with a giggle.

"Oh my god, Finn, I'm so sorry. I didn't even realize!" I stammered as I removed my nails that were embedded in his skin.

"Shh it's ok, I'm just teasing," he said in a calming voice. He kissed my temple and then slowly got out of the bed, pulling a sheet over me as he went.

Making his way to the bathroom, he looked back at me kindly. "You just stay there and relax, okay, Love? I'll be back in a jiff," he said with a wink.

I was in my own little bubble, staring up at the ceiling with a million thoughts and emotions swirling around in my head when Finn returned clad in a fresh pair of boxers. I didn't even notice when he climbed back into the bed on his side, not until he smoothed the hair out on the top of my head and asked: "you ok there Love, are you back on earth yet?".

I heard Finn talking to me and it felt so natural to be lying there with him but then suddenly I had a weird feeling in my gut and it dawned on me that I was still naked underneath the sheet. A wave of uneasiness hit me and I had the urgent need to be covered up.

I looked around the room quickly and spotted my negligee in a heap at the end of the bed, I gestured to it "Finn, could you hand me my nightie please" I asked shyly. He handed it to me and looked the other way as I sat up and pulled it on over my head. Sensing I was done he reached over and hooked the clasps back together for me and rubbed my arm softly "there you go Love, all good now?" he asked cautiously. I nodded and replied "yeah, I'm good, thanks" and we both laid back down.

I laid there for a minute just gathering my thoughts but then I was caught up thinking how sweet, attentive and compassionate Finn was being, and how safe I felt. Within seconds something akin to a magnetic attraction, the warmth of Finn's body calling to me and I couldn't help but turn on my side and snuggle up into him with my head on his chest. He wrapped his arm around me and pulled me in. It made me feel so at peace like I didn't have a care in the world and I just laid there listening to Finn breathing. The last thing I remember was Finn kissing the top of my head before we both nodded off.


	11. 11

**Summary for the Chapter:**

> Finn knows things will be a little awkward now that he and Rory have slept together so he has a little surprise that will help return things to normal.

      After dozing for a little over an hour I woke up with Finn's arms wrapped around me tightly. He was spooning me from behind and besides the fact that it felt so comfortable I couldn't help but snicker at the thought that no one would ever believe me if I told them Finn was a cuddler. As I turned myself in Finn's grasp to look over at the clock behind him I let out a little groan from the stiffness in my body, waking Finn in the process. Returning to my previous position on the bed I was met with Finn's sleepy blue eyes.

I looked down at him "I'm sorry I didn't mean to wake you" I said politely. "It's ok, are you alright love?" he asked in a voice still groggy from sleep. "Yeah I'm good, just a little sore I guess" I replied plainly. We were face to face now and my hand was resting on Finn's arm for support. I looked away as the intimacy of the moment dawned on me and I quickly moved out of Finn's arms and to a seated position. Finn rolled over onto his back sensing my need for a bit of distance.

I felt a little weird and slightly vulnerable being in a slinky negligee in front of Finn now that "it" was over. So in an attempt to break the tension I pulled my overnight bag onto the bed next to me and began rummaging for something to wear. I could feel Finn watching me and I became even more self-conscious. When I couldn't take it anymore I turned and looked at him "this is weird, isn't it? I mean we just had sex. I just lost my virginity and now we're supposed to go back to being friends and act like nothing's happened, how are we supposed to study together... you've seen me naked..it's, it's weird " I babbled.

Finn let out a small laugh "Yes I suppose it is a bit weird Love, but need I remind you of exactly how many times you've seen my naked arse." He pointed out." "You know what, you're right, we can be adults about this, besides Logan will be back in a few days I'm sure that will be distraction enough and I can put all this awkwardness behind me," I said with a small smile. Finn just nodded his head slightly and the faintest of smiles passed over his lips and then vanished.

After a moment of silence Finn shook his head and smiled at me "Now I want you to go and take a nice long hot shower, get into something comfy and when you come out I will have a surprise for you that will make all the awkwardness seem like old news and we can go back to normal, ok." and with that he kissed my forehead and sent me on my way.

As the hot water cascaded over my body and I felt the tension leaving my muscles I let my mind wander back to what had transpired mere hours before. Finn had been so sweet and caring and tending to every need I had, both physically and emotionally. A smirk played across my mouth as I thought of the comment Finn had made about my negligee "you're making this too easy for me" I blushed just thinking about it. I'm pretty sure he said it just to put me at ease, give me a bit of confidence you know but at the same time, it was such a seductive thing to say. He really was an amazing guy, he knew just the right thing to say.

I wondered how Finn was taking this so lightly, maybe because it wasn't his first time. Maybe it really was just "helping out a friend" as he said, but I couldn't help the niggling feeling that there was more to it than that. I decided to just let it go I couldn't complain I had just had really amazing sex and it was only my first time, how many girls can say that. It's like Steph said I lost my virginity to a stallion and now I could be with Logan who is a... what's better than a stallion, oh well, I would find out soon enough.

After approximately 30 minutes of letting the hot shower tend to my stiff muscles and clearing my head at the same time, I dried off and dressed in grey sweatpants and a blue Yale t-shirt. As I exited the bathroom I noticed the candles in the room had been extinguished and the overhead lights were on a dim setting, the only other light was coming from the TV where Finn stood, remote in hand.

As he noticed my presence beside him he turned around "Ah, there you are, feeling better Love?" he asked. "Much better Finn, thanks," I said smiling. Then looking past him I noticed a room service cart off to the side and my eyes lit up with excitement "What's all this, what's going on" I asked gesturing to our surroundings. "This my dear is our 'Ode to Rory Gilmore: Virgin No More' movie night," he said with a huge grin on his face. "We've got desserts galore, nachos, chili cheese fries and of course a pot of coffee. And for entertainment, we have 'The 40-Year-Old Virgin' and all 3 American Pie movies if we so choose. So what do you think?" he asked nervously.

I was so touched I had a hard time finding the words "Finn, this is perfect" I said clutching my hand to my heart.

Finn reached out his hand to me "Come on love" he said leading me over to the bed. "We're going to have a good old fashioned movie night between friends. We'll gorge ourselves on junk food, laugh ourselves silly on stupid movies and I promise if this doesn't work out all the awkward kinks then you never have to see me again. He said, a little too enthusiastically.

I couldn't help the sinking feeling I had in my chest at the sound of his words, it felt like he was trying to convince himself... did he really think we wouldn't be able to be friends anymore? Or maybe he didn't want to be friends anymore, maybe the sex was really bad for him and now he's trying to be nice and not hurt my feelings.

I had to know what was bothering him "Finn is everything ok, you sound a bit anxious or nervous? I asked. "I'm fine Love, why?" he replied nervously. "Well I mean it feels like you might rather just go home, you don't have to do all this, you've already done so much. I just don't want you to feel like we have to spend the night here" I stated simply.

Finn quickly pulled me into his arms, hugging me tightly, then pulling back he looked me in the eyes "Ror, don't be silly you should know me well enough to know that I don't do stuff I don't want to. " he said almost pleadingly and ever so gently stroked his hand along my cheek. Then he licked his lips and took a breath "Now let's get comfy before the coffee gets cold" he said as he directed me to the bed and pulled the coffee cart over to the side of the bed.

Two hours later we had made a significant dent in the nachos, the fries were gobbled up; mostly by Finn, the coffee pot was empty and I ate 3 of the 4 various desserts that had been ordered and true to his word Finn made sure I got my chocolate molten lava cake; I guess it's true what they say: sex does make you hungry.

The movie had just ended, and finally sated; I gave in to the exhaustion I was feeling. Deciding to call it a night, Finn pulled the decorative throw from the foot of the bed up to cover us. Kissing me sweetly on the forehead he said good night and then closed his eyes to let sleep take over.

I laid there for a while staring up at the ceiling, just trying to process everything that had happened that day. Finally feeling my eyelids get heavy I turned on my side, I grazed over the sight of Finn laying there peacefully, fast asleep, the light from the moon casting shadows on his face and I didn't think twice before I kissed him chastely on the lips and curled up under his arm with my head on his chest.

The next morning I woke to the sound of Finn singing in the shower, as always taking any chance to exercise his vocal capabilities; which let's be honest are non-existent. I tried drowning out the sounds so I could get some extra sleep by putting my pillow over my head but to no avail so I decided to get out of bed. In searching for my duffle bag I noticed the room service cart from the night before was gone and a fresh pot of coffee sat untouched on the end table.

I helped myself to a cup and proceeded to get dressed before Finn got out of the shower. I couldn't have timed it better if I had tried because just as I pulled the hem of my t-shirt down over my hips I heard the bathroom door open and there stood a freshly showered and dressed Finn. He looked good and smelled even better, and I had to shake my head to stop myself from giving him a once over.

Surprised that I was already awake and dressed, Finn approached me and kissed the top of my head "morning Love, feel any different this morning? You know you are kind of glowing" he said with a smirk. "I am not, stop that!" I said embarrassed, as he waggled his eyebrows at me.

Wanting to avoid the subject I started to walk towards the bathroom so I could brush my teeth and freshen up. But before I could even take five steps Finn opened his mouth "I'm just kidding Ror, but I think people will figure it out anyway, you are definitely walking a little funny" he said pointing to my legs and the wide stance I was holding. Without a second thought, I whipped my body around and started swatting at Finn until he grabbed me in a bear hug and suppressed my flailing arms.

As he pressed me against his chest I couldn't help but take in a deep breath and inhale his masculine scent letting it fill my senses. God, he smelled so good! It was intoxicating and I could feel him looking down at me. If this was a movie it would be a romantic moment but it couldn't be we were just friends I reminded myself. Then Finn sighed deeply "Now Love before I even think of letting you go you have to promise no more hitting!" he said like a parent reprimanding their 3-year-old. Looking up at him I smiled " I would raise my right hand and swear I won't but your arms are preventing me from doing that so I'll say this; I won't hit if you keep your mouth shut about my 'waddle' ok and that includes Logan of course" I bargained. Finn let out a hearty laugh " Ok you've got a deal Love" he said smiling and finally released me.

I shook my head at him and his childish antics while I giggled to myself as I made my way to the bathroom to complete my morning routine. After I was done I finished up packing my bags. As I crisscrossed back and forth through the room picking up items I caught Finn looking at me a few times, it looked like he had something he wanted to say but when I asked him about it he just told me "nope, I'm good."

We soon made our way out of the hotel and headed to a diner nearby, our conversation strangely limited. Finn had a cheese omelet with bacon and toast while I had blueberry pancakes with eggs and bacon, it seemed my appetite from the night before had returned and unfortunately so had some of my awkward feelings. I was feeling a bit uncomfortable and couldn't seem to keep eye contact with Finn but every so often I would catch Finn looking at me, sometimes with a pensive look on his face other times, it was more like an empty stare.

As I finished up the last bite of pancakes I caught Finn looking at me again but this time he's muttering to himself like he has something to say but can't find the words and all this with a grim look across his face. I was starting to get annoyed, I felt like I was getting mixed messages from him, earlier he was sweet and caring and now he's almost brooding as he stares right through me.

"What is it Finn, do I have whipped cream on my face?" I asked frowning. "Huh, what did you say Love?" Finn replied as he shook his head appearing to come back from the trance he was in. "I asked if I have something on my face, you were staring a hole right through me" I replied with a huff. Finn looked up at me his eyes glazed over slightly " Nope Love nothing on your face, you're all good" he said and gave me a fake smile, I know because I've seen him use it on girls before. What the hell was going on with him I wondered as he seemed to get lost in his thoughts again. I wiped my mouth quickly then grabbed my coat and made a beeline for the cash register.

Taken by surprise by my actions Finn caught up with me by the time I reached the cash register. He took hold of my arm and slowly turned me to face him "what's going on Love, why did you just walk away like that?" he whispered, but before I could answer he added "And what makes you think that you're paying" he smirked trying to keep things light as he produced his wallet from his jacket pocket and paid the bill.

As he was paying I zipped my jacket and proceeded to the front door. Once Finn was done he met me over at the car and unlocked the doors holding mine open for me then placed his hand on the small of my back helping me into the car.

There it is again with the mixed messages.

I don't know what had come over me I could barely look Finn in the eye. I could sense he was trying to break the tension, thinking of any inane topic just to get a reaction out of me.

I got in the car and buckled my seatbelt. Before starting the car Finn looked over at me and placed his hand on top of mine "you wanna tell me what's going on Love?" Avoiding his question completely I moved my hand away and turned to face my window, taking my hint Finn started the engine. After pulling out of the spot he turned the radio on to our favorite punk rock station. As the next song's first chords played Finn nudged my arm "And Go!" he shouted, a wide grin plastered on his face.

We had made up this game a few months back when we were waiting in the car for Logan one afternoon. He was taking longer than the 30 minutes he had promised and both Finn and I were getting antsy. We had turned on the radio and the song Police Truck by the Dead Kennedys was playing. As I mouthed the words Finn looked at me in awe and asked me if I knew that the song was a big part o0f the band's internal conflicts, well of course I did and as I prattled off random information about the song, the band's origins and their ultimate demise he just stared at me in disbelief. "I can't believe you knew all that, I thought I was the only one with a brain full of useless information" he laughed. And thus began our "how-much- random-info-do-you-know-about-this-song-music-trivia-game".

As my mind drifted back to present day I realized that he was hoping I would take the bait. I just looked at him with a half-hearted smile, sorry Finn I'm not really in the mood. I think I'm just going to close my eyes for a bit if that's ok?" I asked not really waiting for his permission. "Sure love, I'll let you know when we're there" he replied with a sad look on his face.

What seemed like only minutes later I opened my eyes to see we had just pulled into the parking lot at Yale.

As Finn put the car in park I undid my seatbelt and was about to open my door when Finn took hold of my arm, grabbing my attention. I turned around to face him "yeah Finn?" I questioned. "Rory, Love, I know something is bothering you and I get it you probably have a million things going on in your head right now but please tell me you aren't going to ignore me for much longer. I get that it's kind of awkward right now but I would hate to lose our friendship over something like this," he asked with a face that matched of a dog left out in the rain. I looked at him solemnly "No, of course not Finn. I just need some time to wrap my head around things. It's all new to me still. "I'll see you in class on Tuesday though right?" I asked hopefully. "Of course silly, where else would I be," he said grinning. I just nodded and kissed his cheek before getting out and making my way to my dorm.

As I made my way into my dorm room I couldn't help but wonder what had gotten into Finn and then also why did it matter? He wasn't my boyfriend and this was his offer to begin with so why was I getting all bent out of shape over it. Whatever was going on would rectify itself in time, and as for me, well I had Logan coming home in a few days which was the whole point of this weekend anyway so I would just focus my thoughts on that.


End file.
